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Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions

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Published in Tetrahedron. 2007, vol. 63, no. 35, p. 8413-8419
Abstract The synthesis of the chiral ligand (R,R)-BIPHOP-F is detailed. Its coordination to a cationic cyclopentadienyl ruthenium fragment generates [Ru (acetone)(R,R)-BIPHOP-F)Cp][SbF6], a transition metal Lewis acid that catalyzes the [3+2] dipolar cycloaddition reaction between aryl nitrile oxides and α,β-unsaturated aldehydes to give chiral 2-isoxazolines with yields of 43–98% and asymmetric purity of 60–93% ee. The stereochemistry of the major enantiomer is S, consistent with an approach of the nitrile oxide to the Cα-Si face of the enal in the anti-s-trans conformation in the catalyst site.
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BRINKMANN, Yasmin et al. Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions. In: Tetrahedron, 2007, vol. 63, n° 35, p. 8413-8419. https://archive-ouverte.unige.ch/unige:7057

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Deposited on : 2010-06-18

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